KR20150002635A - 방사선 경화성 (메트)아크릴화 화합물 - Google Patents
방사선 경화성 (메트)아크릴화 화합물 Download PDFInfo
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- KR20150002635A KR20150002635A KR20147027388A KR20147027388A KR20150002635A KR 20150002635 A KR20150002635 A KR 20150002635A KR 20147027388 A KR20147027388 A KR 20147027388A KR 20147027388 A KR20147027388 A KR 20147027388A KR 20150002635 A KR20150002635 A KR 20150002635A
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- South Korea
- Prior art keywords
- compound
- meth
- acrylate
- acrylated
- acrylic
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 300
- 230000005855 radiation Effects 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 145
- -1 cyclic ether polyol Chemical class 0.000 claims abstract description 140
- 229920005862 polyol Polymers 0.000 claims abstract description 70
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 32
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 28
- 238000000576 coating method Methods 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 239000002966 varnish Substances 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 81
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000945 filler Substances 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 150000001261 hydroxy acids Chemical class 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 13
- 150000002596 lactones Chemical class 0.000 claims description 13
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229960002479 isosorbide Drugs 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 150000003951 lactams Chemical class 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 claims description 2
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 claims description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
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- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 2
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- 238000012360 testing method Methods 0.000 description 14
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 13
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
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- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 8
- 235000013305 food Nutrition 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 8
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- 150000001491 aromatic compounds Chemical class 0.000 description 6
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Resins (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261617870P | 2012-03-30 | 2012-03-30 | |
| US61/617,870 | 2012-03-30 | ||
| EP12171575.9A EP2644589A1 (fr) | 2012-03-30 | 2012-06-12 | Composés acrylés durcissables par rayonnement (méth) |
| EP12171575.9 | 2012-06-12 | ||
| US201361771233P | 2013-03-01 | 2013-03-01 | |
| US61/771,233 | 2013-03-01 | ||
| PCT/EP2013/056137 WO2013144033A1 (fr) | 2012-03-30 | 2013-03-22 | Composés (méth)acrylés durcissables sous rayonnement |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150002635A true KR20150002635A (ko) | 2015-01-07 |
Family
ID=46298265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20147027388A KR20150002635A (ko) | 2012-03-30 | 2013-03-22 | 방사선 경화성 (메트)아크릴화 화합물 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9109137B2 (fr) |
| EP (2) | EP2644589A1 (fr) |
| JP (1) | JP6240151B2 (fr) |
| KR (1) | KR20150002635A (fr) |
| CN (1) | CN104203900B (fr) |
| CA (1) | CA2863490A1 (fr) |
| ES (1) | ES2687020T3 (fr) |
| TW (1) | TWI589615B (fr) |
| WO (1) | WO2013144033A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10427753B1 (en) * | 2017-10-04 | 2019-10-01 | James Patrick Monahan | Method and apparatus for securing foot to pedal with strap secured to axle |
| KR20200078735A (ko) * | 2018-12-21 | 2020-07-02 | 주식회사 제일화성 | 아이소소바이드 기반의 광경화형 조성물 및 그 제조방법 |
| KR102215408B1 (ko) * | 2019-11-12 | 2021-02-16 | 조광페인트주식회사 | 폴리염화비닐 바닥재용 광경화형 무광 도료 조성물 및 이를 이용한 폴리염화비닐 바닥재 제조 방법 |
| KR20220080769A (ko) * | 2020-12-07 | 2022-06-15 | 주식회사 삼양사 | 아크릴-변성 폴리우레탄 조성물 및 그 제조 방법, 및 이로부터 제조된 수계 접착제 조성물 및 그 제조 방법 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2644634A1 (fr) * | 2012-03-30 | 2013-10-02 | Cytec Surface Specialties, S.A. | Composés (méth)acrylés durcissables par rayonnement |
| DE102012219476A1 (de) * | 2012-10-24 | 2014-04-24 | Hilti Aktiengesellschaft | Harzmischung auf Vinylesterurethanharz-Basis und deren Verwendung |
| DE102012219477A1 (de) * | 2012-10-24 | 2014-04-24 | Hilti Aktiengesellschaft | Verfahren zur Herstellung von Vinylesterurethanharzen auf Basis von Dianhydrohexitol-Verbindungen und ihre Verwendung |
| KR102195015B1 (ko) * | 2013-04-26 | 2020-12-28 | 다이셀올넥스 주식회사 | 우레탄 (메트)아크릴레이트 및 활성 에너지선 경화형 수지 조성물 |
| FR3008095B1 (fr) * | 2013-07-08 | 2016-07-01 | Roquette Freres | Nouveaux composes derives de 1:4, 3:6 dianhydrohexitol utiles a la fabrication de polymeres |
| CN107531724B (zh) * | 2015-02-26 | 2020-06-23 | 巴斯夫欧洲公司 | 制备异山梨醇乙氧基化物二甲基丙烯酸酯的方法 |
| WO2016160135A1 (fr) * | 2015-04-03 | 2016-10-06 | Henkel IP & Holding GmbH | Isosorbide étendu de (méth)acrylate fonctionnalisé |
| CN105001826A (zh) * | 2015-07-14 | 2015-10-28 | 苏州科淼新材料有限公司 | 一种耐低温复合材料的制备方法 |
| FR3040059B1 (fr) | 2015-08-13 | 2019-05-17 | Roquette Freres | Utilisation d'une composition d'ethers de bis-anhydrohexitol de faible viscosite comme diluant reactif pour compositions reticulables de resines, d'adhesifs, de revetements et de matrices pour composi |
| CN108368220B (zh) | 2015-10-16 | 2021-05-25 | 汉高知识产权控股有限责任公司 | 由可再生源制成的反应性树脂 |
| EP3184565A1 (fr) * | 2015-12-22 | 2017-06-28 | Allnex IP S.à.r.l. | (méth)acrylates d'uréthane durcissables par rayonnement avec des groupes isocyanates résiduels |
| EP3455264A4 (fr) | 2016-05-13 | 2020-05-20 | MSI Coatings Inc. | Système et procédé d'utilisation d'une composition exempte de cov durcissable par le rayonnement uv d'une del à faible flux de rayonnement |
| CN105949873A (zh) * | 2016-06-15 | 2016-09-21 | 安徽有通玻璃有限公司 | 一种有机玻璃加工用固化油墨 |
| CN105885539B (zh) * | 2016-06-23 | 2018-09-21 | 佛山市彩贵新型材料有限公司 | 一种可用于陶瓷表面喷涂的油墨及其制备方法 |
| CN105907165B (zh) * | 2016-06-23 | 2018-09-21 | 佛山市彩贵新型材料有限公司 | 用于陶瓷表面打印喷涂的组合物及其制备和应用方法 |
| EP3269754A1 (fr) * | 2016-07-12 | 2018-01-17 | Allnex Belgium S.A. | Composés (méth)acrylés à base de pet recyclé |
| US11338320B1 (en) | 2018-02-03 | 2022-05-24 | MSI Coatings Inc. | Composition for aerosol cans, method of making and using the same |
| US10544158B1 (en) | 2019-03-14 | 2020-01-28 | Covestro Llc | Process for producing polycyclic polyether polyols |
| US11566145B2 (en) | 2019-03-14 | 2023-01-31 | Covestro Llc | Polyurethane coating compositions and their use as gel coats |
| DE102019125777A1 (de) * | 2019-09-25 | 2021-03-25 | Schock Gmbh | Wärmeaushärtbare biobasierte Gießmasse, hieraus hergestellter Formkörper sowie Verfahren zur Herstellung eines solchen Formkörpers |
| TWI724765B (zh) * | 2020-01-21 | 2021-04-11 | 達興材料股份有限公司 | 可雷射離型的組成物、其積層體和雷射離型方法 |
| CN111320902B (zh) * | 2020-04-13 | 2021-11-23 | 佛山市儒林化工有限公司 | 一种印铁食品罐外包装用低甲醛迁移光油及其制备方法 |
| KR102449425B1 (ko) * | 2020-06-17 | 2022-10-04 | 주식회사 삼양사 | 친수성 아크릴-변성 폴리우레탄 및 그 제조 방법, 및 이로부터 제조된 수계 도료 조성물 및 그 제조 방법 |
| CN113817086B (zh) * | 2021-09-29 | 2022-11-11 | 韦尔通(厦门)科技股份有限公司 | 一种生物基光固化树脂组合物及其制备方法和应用 |
| CN116086935B (zh) * | 2023-04-10 | 2023-06-16 | 四川公路桥梁建设集团有限公司 | 一种温缩断裂强度测试方法和测试装置 |
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| US20020013482A1 (en) * | 2000-07-13 | 2002-01-31 | Consortium Fur Elektrochemische Industrie Gmbh | Process for the preparation of dianhydrohexitol bis(4-acryloyloxy)acylates |
| WO2007120459A2 (fr) * | 2006-03-31 | 2007-10-25 | E. I. Du Pont De Nemours And Company | Composés chiraux et compositions à base de cristaux liquides et réseaux polymères dérivés |
| US20100136347A1 (en) * | 2006-08-07 | 2010-06-03 | Simons J Brandon Simons | Two component solventless polyurethane laminating adhesives based on 1,4:3,6 dianhydrohexitols |
| JP2011145330A (ja) * | 2010-01-12 | 2011-07-28 | Sumitomo Chemical Co Ltd | 位相差フィルム |
| WO2011128382A1 (fr) * | 2010-04-14 | 2011-10-20 | Bayer Materialscience Ag | Dispersions aqueuses de polyuréthane-polyurée |
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| DE10033512A1 (de) | 2000-07-11 | 2002-01-24 | Solutia Austria Gmbh Werndorf | Aliphatisch niedermolekulare Polyesterpolyole, deren Herstellung und Verwendung in hochwertigen Beschichtungsmitteln |
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-
2012
- 2012-06-12 EP EP12171575.9A patent/EP2644589A1/fr not_active Withdrawn
-
2013
- 2013-03-22 US US14/372,383 patent/US9109137B2/en active Active
- 2013-03-22 EP EP13713132.2A patent/EP2831032B1/fr active Active
- 2013-03-22 ES ES13713132.2T patent/ES2687020T3/es active Active
- 2013-03-22 CA CA2863490A patent/CA2863490A1/fr not_active Abandoned
- 2013-03-22 JP JP2015502249A patent/JP6240151B2/ja active Active
- 2013-03-22 CN CN201380011372.8A patent/CN104203900B/zh active Active
- 2013-03-22 KR KR20147027388A patent/KR20150002635A/ko not_active Application Discontinuation
- 2013-03-22 WO PCT/EP2013/056137 patent/WO2013144033A1/fr active Application Filing
- 2013-03-29 TW TW102111476A patent/TWI589615B/zh active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020013482A1 (en) * | 2000-07-13 | 2002-01-31 | Consortium Fur Elektrochemische Industrie Gmbh | Process for the preparation of dianhydrohexitol bis(4-acryloyloxy)acylates |
| WO2007120459A2 (fr) * | 2006-03-31 | 2007-10-25 | E. I. Du Pont De Nemours And Company | Composés chiraux et compositions à base de cristaux liquides et réseaux polymères dérivés |
| US20100136347A1 (en) * | 2006-08-07 | 2010-06-03 | Simons J Brandon Simons | Two component solventless polyurethane laminating adhesives based on 1,4:3,6 dianhydrohexitols |
| JP2011145330A (ja) * | 2010-01-12 | 2011-07-28 | Sumitomo Chemical Co Ltd | 位相差フィルム |
| WO2011128382A1 (fr) * | 2010-04-14 | 2011-10-20 | Bayer Materialscience Ag | Dispersions aqueuses de polyuréthane-polyurée |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10427753B1 (en) * | 2017-10-04 | 2019-10-01 | James Patrick Monahan | Method and apparatus for securing foot to pedal with strap secured to axle |
| KR20200078735A (ko) * | 2018-12-21 | 2020-07-02 | 주식회사 제일화성 | 아이소소바이드 기반의 광경화형 조성물 및 그 제조방법 |
| KR102215408B1 (ko) * | 2019-11-12 | 2021-02-16 | 조광페인트주식회사 | 폴리염화비닐 바닥재용 광경화형 무광 도료 조성물 및 이를 이용한 폴리염화비닐 바닥재 제조 방법 |
| KR20220080769A (ko) * | 2020-12-07 | 2022-06-15 | 주식회사 삼양사 | 아크릴-변성 폴리우레탄 조성물 및 그 제조 방법, 및 이로부터 제조된 수계 접착제 조성물 및 그 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2863490A1 (fr) | 2013-10-03 |
| ES2687020T3 (es) | 2018-10-23 |
| EP2831032A1 (fr) | 2015-02-04 |
| JP6240151B2 (ja) | 2017-11-29 |
| EP2644589A1 (fr) | 2013-10-02 |
| CN104203900B (zh) | 2016-10-05 |
| JP2015520122A (ja) | 2015-07-16 |
| EP2831032B1 (fr) | 2018-06-13 |
| WO2013144033A1 (fr) | 2013-10-03 |
| US20150005408A1 (en) | 2015-01-01 |
| CN104203900A (zh) | 2014-12-10 |
| TW201345943A (zh) | 2013-11-16 |
| US9109137B2 (en) | 2015-08-18 |
| TWI589615B (zh) | 2017-07-01 |
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Legal Events
| Date | Code | Title | Description |
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| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |